![]() | |
![]() | |
Names | |
---|---|
IUPAC name
(2S)-3′,5,7-Trihydroxy-4′-methoxyflavan-4-one
| |
Systematic IUPAC name
(2S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one | |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.007.538 |
EC Number |
|
KEGG | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C16H14O6 | |
Molar mass | 302.282 g·mol−1 |
Melting point | 226–228 °C (439–442 °F; 499–501 K) |
Solubility in other solvents | Sol. EtOH, alkalis |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Hesperetin is the 4'-methoxy derivative of eriodictyol, a flavanone. [1] The 7-O-glycoside of hesperetin, hesperidin, is a naturally occurring flavanone-glycoside, the main flavonoid in grapefruits, lemons, and sweet oranges. [1] [2]
Various glycosides of hesperetin are known, including hesperidin (hesperetin-7-O-rutinoside), a water-insoluble flavonoid glycoside with low water solubility, [3] Hesperidin is found in citrus fruits and upon ingestion it releases its aglycone, hesperetin. Neohesperidin is the 7-O- neohesperidoside of hesperetin.
Hesperidin 6-O-α-L-rhamnosyl-β-D-glucosidase is an enzyme that uses hesperidin and H2O to produce hesperetin and rutinose. [1] Upon digestion in the gastrointestinal tract, hesperetin – as for all flavonoids – is rapidly metabolized in intestinal and liver cells, releasing smaller metabolites into the blood and urine for excretion. [1] The biological effects of such metabolites in vivo are unknown.
In vitro, hesperetin may affect the slow inactivation phase of inward sodium current channels, and therefore could be used as a template to develop drugs against cardiac arrhythmias. [4] Hesperetin also inhibits TRPM3 channels in vitro. [5]
![]() | |
![]() | |
Names | |
---|---|
IUPAC name
(2S)-3′,5,7-Trihydroxy-4′-methoxyflavan-4-one
| |
Systematic IUPAC name
(2S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one | |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.007.538 |
EC Number |
|
KEGG | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C16H14O6 | |
Molar mass | 302.282 g·mol−1 |
Melting point | 226–228 °C (439–442 °F; 499–501 K) |
Solubility in other solvents | Sol. EtOH, alkalis |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Hesperetin is the 4'-methoxy derivative of eriodictyol, a flavanone. [1] The 7-O-glycoside of hesperetin, hesperidin, is a naturally occurring flavanone-glycoside, the main flavonoid in grapefruits, lemons, and sweet oranges. [1] [2]
Various glycosides of hesperetin are known, including hesperidin (hesperetin-7-O-rutinoside), a water-insoluble flavonoid glycoside with low water solubility, [3] Hesperidin is found in citrus fruits and upon ingestion it releases its aglycone, hesperetin. Neohesperidin is the 7-O- neohesperidoside of hesperetin.
Hesperidin 6-O-α-L-rhamnosyl-β-D-glucosidase is an enzyme that uses hesperidin and H2O to produce hesperetin and rutinose. [1] Upon digestion in the gastrointestinal tract, hesperetin – as for all flavonoids – is rapidly metabolized in intestinal and liver cells, releasing smaller metabolites into the blood and urine for excretion. [1] The biological effects of such metabolites in vivo are unknown.
In vitro, hesperetin may affect the slow inactivation phase of inward sodium current channels, and therefore could be used as a template to develop drugs against cardiac arrhythmias. [4] Hesperetin also inhibits TRPM3 channels in vitro. [5]